Jake Flynn

Observer
DISC Type : ci

Director Sales Engineering at Pentera

Rockwall, Texas, United States

Overview

Jake Flynn is the Director of Sales Engineering at Pentera, where he has risen through the ranks from his initial role as a Sales Engineer. He holds a Bachelor of Science from Wentworth Institute of Technology and a Six Sigma Green Belt certification, underscoring a strong technical and process-oriented foundation that began with his early career as an R&D Engineer.

His career path is distinguished by a significant transition from electro-mechanical R&D in the medical device industry to a leadership position in cybersecurity sales.

Personality Overview

Curious

Value Driven

Example Seeker

They can sound friendly and charming but can quickly change gears to become inquisitive and probing.  They are likely to ask many questions and look heavily for supporting information. They are generally good communicators and can be hard to convince.

Topics They Care About

Automated Security Validation
His role and social posts focus on Pentera's core mission of moving beyond theoretical security to continuously tested and validated security postures.
Cloud Security
He is actively promoting the launch and capabilities of Pentera's new cloud-focused security solutions, indicating a key area of focus for the company.
Sales Engineering Leadership
His career progression at Pentera from an individual contributor to a Director demonstrates a focus on leading and developing technical sales teams.

Media Appearances

Jake has no verified media appearances

Work History

7-2025
Director Sales Engineering at Pentera
6-2022 - 8-2025
Sales Engineer Manager/Team Lead at Pentera
8-2021 - 6-2022
Sales Engineer at Pentera
10-2019 - 8-2021
Solutions Engineer, Carbon Black Security Business Unit at VMware
9-2017 - 9-2019
R&D Engineer, Electro-mechanical at Cardinal Health

Education

2013 - 2017
Bachelor of Science (B.S.) from Wentworth Institute of Technology

More Information

Social Presence :

Prographics :

Exp : 9 Location : Rockwall, Texas, United States Job Level : Mid-senior Designation : Director Sales Engineering at Pentera
URL has been copied!

Insights For Selling To Jake

During A Call Or A Meeting

DO's

  • Share testimonials from known people and give multiple examples of product value
  • Focus on immediate action-items rather than the larger goals
  • Invite them for a social do but don’t rely solely on the relationship

DONT's

  • Don’t be too objective but make sure to pad your storytelling with data points
  • Don’t rely excessively on your relationship with them to win the deal
  • Avoid making offhand commitments

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jake is

  • Proven value, strong testimonials are important to them, relationships will have some weightage.
  • Will you ever get a clear answer from Jake

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Jake move?

  • They like to be detailed and take their time to arrive at decisions.
  • Can Jake take some risk or not?

  • They evaluate their decisions systematically and are less likely to take risks.

You And Jake

Personality Compatibility


Other Pentera Employees

Explore more public profiles from related professionals at the same organization.

More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.